3-(4-Methyl­phen­yl)-2-thioxo-1,3-thia­zolidin-4-one

aDepartment of Chemistry, Government College University, Lahore, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 July 2010;accepted 25 July 2010;online 31 July 2010)

In the title compound, C10H9NOS2, the toluene group and the 2-thioxo-1,3-thia­zolidin-4-one unit are planar with r.m.s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between them is 71.20 (9)°. In the crystal, the mol­ecules are stabilized through inter­molecular C—H⋯O contacts, forming polymeric sheets extending parallel to the (01) plane. C—H⋯π contacts also occur.

In continuation to synthesize various derivatives of 2-thioxo-1,3-thiazolidin-4-one, the title compound (I, Fig. 1) is being reported.

The crystal structure of (II) 3-(2-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (III) 3-(3-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009b) have been published which differ from (I) due to the position of methyl group.

In (I), the toluene group A (C1—C7) and group B (N1/C8—C10/S1/S2/O1) of 2-thioxo-1,3-thiazolidin-4-one moiety are planar with maximum r. m. s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between A/B is 71.20 (9)°. This value is different from 84.44 (9)° and 83.30 (3)° as observed in (II) and (III), respectively. The molecules are stabilized in the form polymeric sheets due to C—H···O type of intermolecular H-bondings and C—H···π contacts (Table 1). The polymeric sheets extend parallel to the (0 1 1) plane (Fig. 2).

In continuation to synthesize various derivatives of 2-thioxo-1,3-thiazolidin-4-one, the title compound (I, Fig. 1) is being reported.

The crystal structure of (II) 3-(2-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (III) 3-(3-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009b) have been published which differ from (I) due to the position of methyl group.

In (I), the toluene group A (C1—C7) and group B (N1/C8—C10/S1/S2/O1) of 2-thioxo-1,3-thiazolidin-4-one moiety are planar with maximum r. m. s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between A/B is 71.20 (9)°. This value is different from 84.44 (9)° and 83.30 (3)° as observed in (II) and (III), respectively. The molecules are stabilized in the form polymeric sheets due to C—H···O type of intermolecular H-bondings and C—H···π contacts (Table 1). The polymeric sheets extend parallel to the (0 1 1) plane (Fig. 2).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Acknowledgements

DS is grateful to the Higher Education Commission (Pakistan) for funding this project and Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

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